This goal of this research is the development of a new method for the stereocontrolled synthesis of secondary alcohols, acylic aliphatic amines, 1,2-diols, 1,2-amino alcohols, and 1,2-diamines. Such motifs are found in compounds of biological and medicinal importance, the drugs Taxol, vancomycin, and indinivar being notable examples. The method will allow for the formation of these compounds directly from primary alcohols and acylic aliphatic amines, starting materials which are abundant and widely accesible. It is envisioned that the technologies developed in this program will find use in the synthesis of natural and unnatural therapeutic agents; this will be demonstrated by the application of these methods to the total synthesis of the Strychnos alkaloid (-)-dehydrotubifoline. A portion of the research will examine the development of asymmetric C-H bond activation processes, an area of chemistry which is still largely unexplored. [unreadable] [unreadable] [unreadable]